1,3,5-Triaza­adamantan-7-amine

Thomson, J.; Chisholm, D.M.; Oliver, A.G.; McIndoe, J.S.

doi:10.1107/S1600536810037657

Volume 66
Part 10
Page o2637
October 2010

Received 16 September 2010
Accepted 20 September 2010
Online 25 September 2010

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.001 Å
R = 0.039
wR = 0.122
Data-to-parameter ratio = 18.5
Details

1,3,5-Triazaadamantan-7-amine

Jaclyn Thomson,^a Danielle M. Chisholm,^a Allen G. Oliver ^b ^* and J. Scott McIndoe ^a ^*

^aDepartment of Chemistry, University of Victoria, PO Box 3065, Victoria, BC V8W 3V6, Canada, and ^bUniversity of Notre Dame, Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA
Correspondence e-mail: aoliver2@nd.edu, mcindoe@uvic.ca

The title compound, C₇H₁₄N₄, represents the first structurally characterized, isolated triazaadamantane. In the crystal structure, weak intermolecular N-HN hydrogen bonds link the molecules into columns about the crystallographic fourfold axis.

Related literature

For general background to applications of the title compound and its preparation, see: Hodge (1972); Karelina et al. (1987); Kuznetsov et al. (2001); Nielsen (1975, 1977); Safar et al. (1975). For related structures, see: de Namor et al. (2008).

Experimental

Crystal data

C₇H₁₄N₄
M_r = 154.22
Tetragonal, P 4₂ /n
a = 15.5402 (8) Å
c = 6.5074 (7) Å
V = 1571.5 (2) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 150 K
0.32 × 0.24 × 0.15 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: numerical (SADABS; Sheldrick, 2008a) T_min = 0.973, T_max = 0.987
15555 measured reflections
1960 independent reflections
1662 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.122
S = 1.52
1960 reflections
106 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N11-H11AN3ⁱ	0.898 (12)	2.335 (13)	3.2316 (13)	176.0 (12)
N11-H11BN11ⁱⁱ	0.895 (14)	2.253 (14)	3.1465 (14)	175.2 (11)
Symmetry codes: (i) x, y, z-1; (ii) $[-y+{\script{3\over 2}}, x, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: XP (Sheldrick, 2008b) and POV-RAY (Cason, 2003); software used to prepare material for publication: XCIF (Sheldrick, 2008b) and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2767 ).

Acknowledgements

Data were recorded on an instrument supported by the National Science Foundation, Major Research Instrumentation (MRI) Program under grant No. CHE-0521569.

References

Bruker (2005). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA.
Cason, C. J. (2003). POV-RAY. Persistence of Vision Raytracer Pty Ltd, Victoria, Australia.
Hodge, E. B. (1972). J. Org. Chem., 37, 320-321.
Karelina, V. N., Goncharov, V. M., Mirontseva, T. V., Delektorskii, A. A. & Orekhov, S. V. (1987). USSR Patent SU1359277, December 12, 1987.
Kuznetsov, R. M., Balueva, A. S., Serova, T. M. & Nikonov, G. N. (2001). Russ. J. Gen. Chem. 71, 899-902.
Namor, A. F. D. de, Nwogu, N. A., Zveitcovich-Guerra, J. A., Piro, O. E. & Castellano, E. E. (2008). J. Phys. Chem. B., 113, 4775-4780.
Nielsen, A. T. (1975). J. Heterocycl. Chem. 12, 161-164.
Nielsen, A. T. (1977). 7-(N-Methyl-N-Alkylamino)-1,3,5-Triazaadamantanes. US Patent 4012384, March 15, 1977.
Safar, M., Galik, V., Kafka, Z. & Landa, S. (1975). Collect. Czech. Chem. Commun. 40, 2179-2182.
Sheldrick, G. M. (2008a). SADABS University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds